The more challenging stipulation is you would need to use it more than 50% of the time for business use (and you need to log the miles to document that).  

That process has direct lender involvement.Where the challenge lies, is when unsophisticated "investors" with no experience, no money and no reserves use creative financing (often called wrap, subto, lease option, seller financing, land contract) to purchase properties and along the way there is a "hiccup".

You don't have to have water & sewer lines in the ground to approach a homebuilder company but you will have to have lots and layout drawn to get any type of commitment.

What are the biggest challenges people have faced with this.

Your first clue will be how they approach showings.

Although I agree with @Nathan Gesner in part, I think he is off base in categorizing a relationship based approach to landlording as "amateur".

there you go. the problem is appraisal. comparable sales, and your approach to building an ADU against the recommendation of your market. super beginner strategy it's popular in ohio as well but just not worth the investment. 

While I own quite a few rental units already, I thought condos might be a good option to gift to my kids when they turn 18, offering them a safe introduction to property ownership without too much risk.However, my challenge with investment condos is that the cash flow always seems terrible.

People all of the time, "over estimate" the opportunity and "underestimate" the cost and challenges in doing a profitable flip.

Hi everyone, I recently purchased a rental property in a condo managed by an HOA, and I’m dealing with a challenging situation that I’d appreciate advice on.